


Paying off Debts

by Bella_Monoxide



Series: The Adventures of Dean Winchester, Scam Artist Extraordinaire [2]
Category: Supernatural, The Walking Dead (TV)
Genre: Anal Fingering, Anal Sex, Blow Jobs, Dean is too full of himself, Hand Jobs, Kissing, M/M, Sex in a Car, gambling debts are debts of honour, poker games
Language: English
Status: Completed
Published: 2016-06-27
Updated: 2016-06-27
Packaged: 2018-07-18 16:25:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,425
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7322368
Author URL: https://archiveofourown.org/users/Bella_Monoxide/pseuds/Bella_Monoxide
Summary: <blockquote class="userstuff">
              <p>Daryl Dixon uses all his considerable skills to try and get into Dean Winchester's pants.</p>
            </blockquote>





	Paying off Debts

**Author's Note:**

  * For [pharmtechgirl71](https://archiveofourown.org/users/pharmtechgirl71/gifts).



> Though this is part of a series, it can be read as a stand-alone as well. The events take place on the same evening as the ones in "Cashin' In".

Later that day, after some time spent in their hotel room doing research, Dean was bored out of his skull, whereas Sam could have done nothing but research for days and be happy about it. Unlike Dean, Sam seemed to be made for that kind of thing.

Grabbing his head in a desperation that was almost comical to watch, Dean suggested for them to head out to a bar, reminding Sam that they were almost out of cash when his younger brother did not appear to be too keen on heading out again.

Sam even teased Dean, asking if he thought that there were any gay bars in Georgia that he could hit, but Dean did not rise to the bait. Abruptly fed up with all the teasing he had already gotten from Sam since they had made it back from that diner, he simply got up, grabbed his jacket with a shake of his head and asked "You comin' or stayin', Sammy?" - in a voice that clearly indicated he did not care either way.

Grousing under his breath over the nickname, Sam got up and gathered his stuff, then went after Dean who had hopped into the Impala already, his trusted vehicle. If one took Dean's affection for the car into account, the nickname 'Baby' had been chosen with unerringly accurate precision.

Soon, they arrived at one of the dingy bars in town and headed inside, Sam to continue his research, while Dean was hell-bent on making some money via poker. Since his skills were very good, he won a considerable amount of cash over the course of the next couple of hours, while Sam sat in a corner in the back, quietly nursing a beer or two, as he followed several leads on his trusted laptop.

"Not the best place to have a pricey device like that out in the open," a gravelly voice rasped too close to Sam's ear, and his head shot up to determine if he was being threatened.

The man had the built of a boxer, and he looked battle-scarred enough to actually have been one in his youth. His hair was gray, shaved down to a buzz cut, and he cackled loudly now, amused over Sam's reaction.

Sitting down next to Sam, he slammed his own beer on the table and said "Not talking 'bout me, Sam, but there's a lot of low-lifes hanging around here, so I thought I'd warn you, since we're colleagues, a'ight?"

One of his shovel like hands slammed down on Sam's shoulder, and the younger Winchester winced from the impact. When he inquired in a low voice as to what the guy was even talking about, trying to keep up a front of being just another busy student, the man got serious, all joviality suddenly gone.

His eyes narrowed to small slits, he leaned even closer and whispered in a voice that bordered on threatening "Listen carefully now, Winchester, you might be able to pull the wool over people's eyes, but not us, your fellow hunters, understood?"

Leaning back in his chair, he took a slow sip from his beer before he continued "You and your brother," he shook his head, "you got some nerve. Waltzing into this state, knowing nothing 'bout anything, but here you are, expecting me to take some lip from you? Forget it."

Sam, more than fed up by then, hissed "Who are you even? And what did you mean, 'you'?" He put airquotes around the word, while he grinned mockingly. "Are you always talking in multiplicity? Maybe you should go see a doctor then. Sounds to me like you took one too many to the head."

The older man simply belted out a round of laughter, then held his beer out for Sam to clink with his own bottle, before he said by introduction "Merle. Merle Dixon." He cackled again, then added "Was talking about me 'n my baby brother, of course."

Rolling his eyes, Sam took a sip from his beer and asked "And that would be... who, exactly?"

Merle's face shut down like a clam, as he added with an air of secrecy "That would be the guy your brother is going to lose all his winnings to as we speak."

About to protest, Sam did not get the chance to voice his opinion of Dean's poker skills, as Merle shook his head and simply talked as if Sam had no say in the matter. "Believe me, boy, your brother is in way over his head – just like this afternoon." He added that last remark with a sly expression, and he was not disappointed.

Sam reacted with utter disbelief, which prompted Merle to explain some more. "We were at that diner your brother and you had dinner at as well, and let's just say that the owner would be real pleased if your cute brother with those pouty lips of his would drop in again sometime, preferably without a valid credit card."

Grinning, Merle drank more beer, waiting patiently while Sam defended his brother. When he had to stop for air, Merle shook his head, looked at him pityingly and patted his arm.

"No need to get your panties in a twist over that, Sam, but stop denying your brother's fairy tendencies, a'ight? So," he added, speaking resolutely over Sam's protest, "Where 're you at, hunting those vampires you're after?" Merle asked conversationally, changing the topic to business just like that.

Sam gulped. Stared. Then began to talk.

* * *

Meanwhile at the other end of the bar, Daryl Dixon had been edging closer towards the poker tables, all the time keeping an eye out for the older Winchester brother, but careful though not to make it too obvious. As opposed to the brothers, he had grown up in Georgia and knew the people too well for his own liking – especially when it came to gay men.

Observing the process of the games, he thought about how lucky he was to have picked the same bar the Winchesters had chosen for the night, as Dean's mumbled remark about loosing his last poker money to pay for that piece of pie was still stuck in the younger Dixon's ear.

Being the quiet observer he was, he had checked Dean out, under the cover of his brother Merle's constant chatter, and liked what he saw a lot. Later on, he had mentioned that poker reference to his brother, when they had spotted the Winchesters in the bar, and Merle had laughed, stating that Daryl could easily take all of Dean's winnings away just as quickly as he had made them.

Of course that had prompted Daryl to comment on how much Martinez would like for Dean not to be able to pay for the second time around, which caused a laughing fit out of Merle, who wheezed out for Daryl to go ahead and get at it, while he strolled over to the younger brother. Calling after Merle to go easy on Sam, Daryl got flipped off playfully by his brother, grinned, and walked over to the spot he was located at now.

Thinking how he had successfully managed to not let on how much he liked the looks of the older Winchester brother, Daryl made up his mind and walked over to the table Dean was sitting at, tapped his current opponent on the shoulder and leaned down to talk quietly into his ear.

"I would stop now, if I were you, Axel." When the blond guy with the waxed mustache turned his head to look at him questioningly, Daryl continued to explain. "I doubt that your missus would appreciate it if you lost all your housekeeping money for the month in a game of cards, wouldn't you agree..?"

Mortified, Axel nodded, only now realising what he was about to do, since he was not the sharpest knife in the drawer. He quickly ended the game, got up, and Daryl slid down into the vacated seat in one smooth motion that emphasised his bare arms perfectly, since he was dressed in one of his shirts with the sleeves ripped off.

Dean's eyes widened, as he waited for Daryl to speak, which did not go unnoticed, but Daryl took his time staring the older Winchester brother down before he challenged him to a game.

Still assuming that he was the better player, Dean accepted, and they were soon on their way into a suspense-packed game, both players not inclined to give the other even an inch.

Eventually, their third game in a row was nearing its end, and Daryl had made up his mind to suggest an out for Dean, even if he had been planning on taking advantage of the handsome hunter, no matter how their games ended.

He bent forward and whispered over the table only for Dean to hear "You know I will take your money again, dontcha?" When Dean snorted disbelievingly, Daryl carried on, unfazed. "I will. No doubt about it. But," here he paused for effect, "I might be willing to let you keep some money – of course," he added, a smirk playing at the corners of his mouth, "you'd have to come up with some other form of payment instead..."

Leaning back again, Daryl watched with just a hint of amusement, as a whole bunch of different emotions played across Dean's face at his implications. When Dean did not say anything though, Daryl called, and placed his hand on the table for Dean to see.

Defeated yet again, Dean closed his eyes for a moment. When he reopened them, he found that Daryl had silently gotten up and close in the meantime, and was now in the process of pulling Dean up out of his chair.

"Tell you what, Dean," he told him quietly, "I'll buy you a beer now, and we talk, that sound good to you?" He did not wait for an answer, but proceeded as planned, then pulled Dean into one of the many dark corners of the bar.

When they both had taken some gulps of beer each, Daryl leaned in close and asked Dean how he planned on getting out of his predicament, but he laughed when Dean suggested another game between them. "You and me both know how that'll end, Dean." Sobering up quickly, Daryl continued. "Now. Lemme suggest something."

Dean shook his head, but continued to listen, wondering what Daryl might be thinking of. His expression turned to alarmed with Daryl's next question. "How about that Impala you're drivin'?"

Dean's eyes almost popped out of his head, and he shook his head vehemently, clearly determining that his car was off limits.

For a guy that showed little to no expressions, Daryl's face looked almost amused when he leaned over towards Dean and whispered into his ear. "You'd rather pimp your own ass, then? Well." He leaned back against the wall, crossed his arms over his chest in a laid back manner and stated, only loud enough for Dean to hear, "Aren't you the little slut, huh."

His face an alarming shade of red, Dean fumed, turned on his heel – and made it as far as a couple inches before Daryl had caught up with him, one hand clamped firmly down on Dean's upper arm as he leant in to whisper "How 'bout a compromise then."

Dean looked daggers at Daryl, but his stormy blue eyes held Dean's fiery gaze easily. "If you think that'll get me to shiver in my boots, you gotta think again, boy," Daryl whispered, before he shoved Dean to get him going.

Too perplexed by Daryl's unwavering behaviour, Dean walked ahead and out of the bar, towards his car, with Daryl hot on his heels. As Dean got in, Daryl went around the car and got into the passenger seat as soon as Dean had unlocked the door. Daryl gave Dean directions to a spot that ensured them some privacy, and on their way there, Dean curiously asked him a question.

"What did you mean earlier, about your shivering in those boots?" When Daryl cast him a sideways glance, Dean specified some more. "I mean, it sounded like you were referring to something other than just the usual supernatural crap." He paused before he added. "I'm assuming you and your brother are those local hunters Martinez mentioned to me today."

Nodding in confirmation, Daryl looked straight ahead again as he answered. "Yep, you got that one right. Me and my brother, we grew up around here." Daryl sighed audibly before he continued. "We're rednecks, so our family wasn't exactly all about fuzzy feelings and stuff, if you get me drift."

Dean, in the process of parking the car in that secluded spot Daryl had lead him to, shook his head.

Sighing yet again, Daryl rolled his eyes. "Our dad was a mean drunk who used us as his punching bags, 's all."

Faced with Dean's horrified expression, Daryl gave him a small smile. "Was a long time ago. He's dead now, has been for years." A thoughtful silence later, Daryl laughed before he added a juicy detail. "Me and Merle, we even went and defiled his grave soon 's we had the chance."

Dean was still showing signs of shock, and Daryl leaned over, a comforting hand placed firmly on Dean's shoulder. "Don't worry your pretty little head about it."

"Did you just call me pretty..?" Dean asked incredulously, and Daryl rolled his eyes so hard that he feared they might exit his skull.

"Anyone ever told you that denial doesn't suit you too well?" He asked, shaking his head.

Looking over again, he noticed that Dean looked affronted, which caused Daryl to bury his head in his hands, groaning. "Gawd, you're piece of work, Dean," he stated, before he managed to regain the grip on his temper.

"Now about our deal," Daryl began, calm to his core again, and it was Dean's turn to roll his eyes. It did not help him one bit, since Daryl continued "you can roll those pretty green eyes all you like, but that won't help you out, so just listen, a'ight?"

When Dean nodded hesitantly – and not just a little resigned – Daryl suggested his compromise. "As you might have noticed from my first suggestion, I like your ride a lot. So, even if I was joking earlier, I sure wouldn't mind to have a little fun in the backseat of this baby, preferably with you. Whaddaya say to that, Dean?"

Leaning back comfortably, Daryl listened to the litany that tumbled out of Dean's mouth after that, unfazed, until he simply stated some time later, his voice no louder than a whisper, but somehow still clearly audible over Dean's speech. "You know you could already be sucking my cock by now, right?"

That did the trick of shutting Dean up on the spot.

Daryl, not shy, used that moment of silence to his advantage, by leaning forward, grabbing Dean by his shoulders and planting a kiss smack dab on the handsome hunter's full lips. Dean fought him only briefly, before he sighed audibly as he gave in to the kiss.

His hands found their way into Daryl's shaggy hair, and Daryl groaned as he deepened the kiss, his tongue fighting Dean's for dominance. Needless to say, Daryl won that game as well, and he used his advantage to draw the most delicious sounding moans out of Dean, before he broke the kiss to suggest breathlessly "Backseat, now?"

Dean could only nod, and they were both out of the car and into the back in a jiffy, tangled up in each other, grabbing at hair, biceps and shoulders as they went on to kiss each other out of breath.

Yet again it was Daryl who broke contact.

"Lose your shirt, handsome?" He asked Dean, while he grabbed the hem of his own shirt and pulled it over his head, revealing a muscled up torso.

Dean, who had obliged to Daryl's request, stared at the scars that Daryl had inevitably revealed as well, a silent question in his eyes, to which Daryl nodded before he confirmed "Yep, those go way back, cortesy of dear ole dad, though I also got some on me that I compiled in the line of duty, so to say."

He leaned into the backseat under Dean's curious eyes, who watched with his breath held as Daryl opened his belt, popped the buttons on his jeans and pushed his hand inside to grab his rock-hard cock. Dean's eyes widened when he laid eyes on the size for the first time, a notion that did not go unnoticed.

"Like what you see..?" Daryl rumbled suggestively, and he laughed when Dean snorted.

Getting serious again quickly, Daryl grabbed Dean's chin with his other hand to hold his head still, forcing him to watch as Daryl began to jerk himself off with rough strokes, moaning as he did so. Dean licked his lips involuntarily, which caused Daryl to whine. "Come on, Dean," he coaxed, "put that big mouth to good use for once..."

When Dean hesitated for a moment, Daryl groused under his breath "You want me to cum all over the seats?" He almost laughed when he saw himself faced with Dean's shocked expression, clearly envisioning his precious Baby covered in spunk, but managed to add "Well, then you better open up that pretty mouth of yours, and quick."

Seconds later, a deep moan escaped his chest, as Dean had engulfed Daryl's length with his luscious lips, and began to bob his head up and down, his hand placed around what his mouth could not reach.

Daryl held on to Dean's shoulders as he moaned. He had the hardest time not to push his hips up. "Come on, Dean, take me deeper, I know you can..." He tried to spur him on, and Dean hightened his efforts even more, so that the swollen head of Daryl's cock hit the back of Dean's throat with every push, causing Daryl to cry out.

Minutes later, Daryl warned "Imma cum, Dean," right before he shot hot strings of cum down the handsome hunter's throat. Dean swallowed a lot of it accidentally, but managed to wrestle the door open and lean outside, retching as he tried to get at least a portion out and on the ground, when he felt Daryl's hands on his body.

First he assumed that Daryl meant to help him keep his balance, but when he felt deft fingers fiddling with his own pants, Dean was back in the car in a nanosecond, pulling the door close again with an audible bang.

He stared at Daryl, who looked right back, while his hands never stopped – until he had reached his goal. With his hand wrapped around Dean's erection, Daryl smiled at him sweetly before he asked innocently enough "Something wrong, Dean?"

Dean spluttered "But I... This wasn't, I mean..."

Shaking his head, Daryl sighed before he explained "Did you really believe that this was only about me getting off?" When he saw the look on Dean's face, Daryl continued. "Don't get me wrong, I like a good blow job like the next guy, but at the end of the day, mutual satisfaction is the key, wouldn't you agree?"

He successfully prevented Dean from answering that rethorical question though, by starting such a relentless assault on Dean's leaking member that the handsome hunter could only moan helplessly.

Dean held on to Daryl's back while he knelt on the backseat, his legs siding with Daryl's so they were crotch to crotch.

"Dean," Daryl whispered after some time, and when Dean quirked an eye open, Daryl continued "you're beautiful like this, you know that?" Both of Dean's eyes popped open at that, and he looked very much as if he could not believe that Daryl had just said that, when he noticed that he was still talking.

"Can I kiss you again?" Daryl asked almost shyly, his other hand already at the back of Dean's head, and they both bent forward to meet in a series of heated kisses, accompanied by heavy breathing and a lot of moans – on both sides.

Incredulously, Dean realised that Daryl had already gotten hard again, which caused Dean to brake the kiss to look at Daryl questioningly.

Daryl let go of Dean's cock, and he placed his hands on Dean's hips before he asked in a quiet voice "Let me fuck you?"

Dean, surprised that Daryl offered him a choice in the matter, thought about the proposition for a moment, until a thought hit him and he asked "You got any lube? Because," he added, shuddering, "I sure as shit won't let you near me with no lube, with that giant cock of yours."

Daryl laughed so hard that Dean thought he had lost it for a moment. But eventually, Daryl caught himself and dug around in his pants, fishing a small bottle out of a pocket.

A sigh of relief escaped Dean's mouth, which caused Daryl to lean in for another bout of kissing, while his deft fingers found their way to the handsome man's ass, pushing his pants down to feel his way towards that tight back entrance, his fingers now slick with lube.

When the first finger breached that hole, Dean tensed, and Daryl whispered soothingly into his ear while his other hand sneaked around to touch Dean's cock again, cleverly distracting him, so that Daryl was able to continue in his preparations.

Soon enough, Dean's hole was sufficiently stretched, and Daryl pulled a condom out of his pocket. Dean snatched it right out of his hand, opened the wrapper and rolled the rubber down Daryl's length. As soon as he was done, Daryl grabbed his ass-cheeks to position Dean over his raging hard-on, and the handsome hunter began his descent on that impressive cock.

When the head of Daryl's erection hit Dean's hole, Daryl gave Dean's dick another stroke or two, and Dean moaned loudly as he sank down inch by inch, acutely aware of how Daryl filled him up. Finally back in Daryl's lap, Dean swallowed dryly, while Daryl gave him a look of sympathy.

"I know it's much, but just wait how good it'll make you feel in a moment."

Dean shook his head. "Already does," he murmured, then began to lift his ass up, only to sit back down right afterwards, and in a matter of seconds, Daryl was a wanton mess, driven wild by Dean's relentless riding movements.

The car began to vibrate with their motions, but neither Daryl nor Dean noticed much of that, too wrapped up in the moment. Their kisses were heated, but got sloppier the closer they got to their respective orgasms, and it was Dean who caved first, spilling cum all over Daryl's hand and stomach, while he moaned helplessly, his head tucked in the juncture between Daryl's neck and shoulder.

Daryl used his strength to turn Dean around a bit, laid him out on the seat, and fucked him as he held on to his hips with both his hands until he shot his load for the second time that night, crying out loud.

When he felt like he could move again, Daryl pulled out and went to open the door to get rid of the condom. He tucked his equipment back inside while he was already out of the car, then bowed inside to help Dean to his feet as well.

Dean got some Kleenex to clean himself up, then threw out the condom wrapper to get rid of the evidence, and both hunters got their clothes back on, but when Dean made to walk around the vehicle to the driver's side, he saw himself wrapped up into a tight embrace.

"I enjoyed that a lot, Dean," Daryl whispered into his ear, and Dean could not help the sigh that escaped his throat, even though he would deny it until his dying day, and they both knew it.

Parting, Daryl asked almost shyly if Dean would let him drive.

Dean looked at him for the longest time, a debate clearly going on behind those green eyes of his.

Minutes later, the result of said debate caused both Merle and Sam, who by then had stepped outside the bar to wait for their brothers to return, to comment at the same time "Well, I'll be damned."

* * *

They ended up in a different bar for a bite, since Merle had suggested for the four of them to put their heads together, seeing as he and Sam had talked about those vampires the Winchesters were after for some time while Dean and Daryl had gone on their spin.

Daryl had convinced both Sam and his own brother that he had cut Dean some slack, letting him pay back his poker debt to him via a drive around the block in his precious Impala. At the end of the evening, the four hunters parted on good terms with each other.

On the way back to their motel, Sam mused over how he had always thought that Dean might have some hidden bi-tendencies somewhere in him, thinking that it would explain why people frequently assumed that he and Dean were a couple rather than brothers, when Dean interrupted his thoughts.

"What do you think, Sammy? Let's leave first thing tomorrow, this town is way too gay for my liking..."

Dean blushed quite a bit when his younger brother broke out into a laughing fit, not able to stop until they were parked at the motel. Trying hard to catch his breath, Sam explained his thoughts to Dean, who left the car in a huff, but could not stay angry at Sam for too long.

* * *

On the other side of town, Merle and Daryl Dixon sat on their sofa with a last beer each, before they went to bed.

"So," Merle started casually, "how was that ride in Dean Winchester's precious car..?"

Daryl's prompt description of how wonderful of an experience it had been to steer the Impala for some time was interrupted by Merle's lapidary comment "Never mind, baby brother." Merle got up to turn in for the night, mumbling under his breath, but still making sure that Daryl could hear him "I really don't wanna know about that _joyride_ you two took while the car wasn't even moving."

Never again did Daryl assume that he could fool his older brother; he just felt grateful when Merle did not bring Daryl's preferences up again.

 

**Author's Note:**

> Please leave a comment to let me know how you liked the story!


End file.
